Don Kessinger came to my school when I was in second grade. I know this only from a vestigial memory of a very tall man (who was not a priest) signing pictures and Sister Mary Francella handing me one. I still have the picture.

WHO WERE YOU?:

A plump seven-year-old. While batting, I was usually Ernie Banks because you couldn’t honestly copy Billy Williams’s swing. In the field, Glenn Beckert because you got to lay out, which was maybe not always such a graceful thing for a plump seven-year-old.

WORKING ON:

A book about Chicago in the Fifties.

HISTORICAL FIGURE I’D HIRE TO MANAGE THE CUBS:

Ulysses S. Grant. He’d keep throwing people out there all summer until they won and he’d shoot the deserters. Plus, it would be fun to see someone in the dugout nipping at a flask.

THE CUB I’D MOST WANT TO LIVE INDEFINITELY IN MY BASEMENT:

Since I live in an apartment building, that would mean he’d be my Super. In which case, I’m thinking I want somebody handy, a utility guy. So I guess I have to say Paul Popovich.

MOST CHERISHED CUBS MEMORY:

Watching the rebroadcast of the Phillies-Cubs ’79 Slugfest during one of those awful winters. Nothing sums up the Cubs better than replaying a game they LOST in order to cheer people up.

BEST PIECE OF CUBS MEMORABILIA:

My old scorecards from the Seventies, with my lame scorekeeping and the kind of ugly, kind of beautiful covers.

THE CUBS WILL WIN IT ALL IN 2009 BECAUSE:

It was Felix Pie that was holding them back.

THE CUBS WON’T WIN IT ALL IN 2009 BECAUSE:

President Obama (a notorious Southsider) will sign an executive order forbidding it.

I met Jose Cardenal at a Mt. Prospect Jewel in the produce section a few winters ago. I had my two oldest boys with me, and I kept circling the bananas and oranges bin to get a closer look.Jose was trying to pick out the best red onion in the nearby onion bin, examining them all closely. My kids thought I had gone completely out of mind. I finally conjured up the courage to say “Are you Jose Cardenal? Good ol’ #1?” He smiled and shook my hand. You have to understand that I worked as a radio producer for 20 years and met just about every celebrity and it had never affected me before—but I was positively giddy about meeting Jose. I asked him what he was doing there and he said that he never moved out of town. He spends his off seasons in Prospect Heights.I remember thinking, “Prospect Heights should put that in their brochures. A guy from Cuba thinks this place is so cool he spends his winters here.”

WHO WERE YOU?:

In my mind I was always Ernie Banks. In Little League, I was more like the Mick Kelleher of my team.

WORKING ON:

Two new books and a screenplay. A humorous parenting book about raising boys (with my friend, author Kim Strickland), and a novel about 1918 Chicago. The screenplay is a true story about a bank robbery in Milwaukee.

DAY JOBS:

Editor-in-chief of Justonebadcentury.com, columnist/blogger for NWI Parent magazine, media columnist for Chicago Radio Spotlight (chicagoradiospotlight.blogspot.com), and most importantly, stay-at-home dad.

RADIO PERSONALITY I’D HIRE TO MANAGE THE CUBS:

Dick Biondi. He has more energy in his 70-something body than the entire Cubs team combined. Plus, he’s been fired something like 20 times in his radio career. He could take it when that inevitable day came.

THE CUB I’D MOST WANT TO LIVE INDEFINITELY IN MY BASEMENT:

Carmen Fanzone. He could play his trumpet for us at dinner time.

MOST CHERISHED CUBS MEMORY:

That’s probably a three-way tie. I was at the Sandberg game with my little brother. We had standing room tickets and moved around the whole ballpark looking for somewhere to sit. I was also there for Kerry Wood’s 20-strikeout game. My boss at the radio station had just told us they were going to revamp our show (The John Landecker Show), and rather than get all depressed, I took my colleagues to the game and we saw the best pitched game in history. That really took the sting out of it. And then last year I took my youngest boy Sean to a game. He’s six, and he was totally into it, as much as I was at his age (1969). I could just see the torch being passed before my eyes. Sorry, Sean.

BEST PIECE OF CUBS MEMORABILIA:

I have the baseball card of every starter from the 1908 Cubs, including the starting rotation. I told my wife I was buying them to sell on my Web site, and they are available for sale there, but I secretly hope no-one ever buys them.

THE CUBS WILL WIN IT ALL IN 2009 BECAUSE:

They won’t. Although...that lineup is pretty strong, and the rotation could be the best in the league if everything goes right, and I like the back end of the bullpen, and Lou is a great manager, and....Aaaaaaaaargh! I’m doing it again!

Final home game. 1987. Cubs in last place. I’m in the right field bleachers. Andre Dawson hits his 49th home run after a career year and walks out to his positions. He turns to the bleachers and that quiet, stoic MVP genuflects to the fans in the bleachers. Dramatic and unexpected.

My wife entered me in some Com Ed contest, and I won. Me, my brother and Flynn got to do a tour of the park before the game, and they took us to the batting cage under the right field bleachers. Billy Williams was in there, pitching to his grandson. It was pretty magical, like seeing a unicorn or something.

What player did you pretend you were as a kid?

Ron Santo.

Working on?

An illustrated blog, Cubby-Blue.

Day jobs?

Advertising.

Artist I'd hire to manage the Cubs?

I would ask Lou Piniella to paint a painting.

The Cub I'd most want to live indefinitely in my basement?

Creepy question. Maybe Don Zimmer, just to scare the kids.

Most cherished Cubs memories?

Bleachers in the ‘80’s, the Sandberg game, 2003 (still the greatest season in my lifetime), and the breathless phone call I got from my brother when he just said, “Turn on a TV, Wood has 17 strikeouts.”

Best piece of Cubs memorabilia?

Not really a memorabilia guy…My family got me one of those bricks outside Wrigley. I still haven’t found it, but I intend to - it means a lot to me.

And maybe this T-shirt I made in the late 90’s that says “Cub Fan” on the front and “Kick Me” on the back. (I only made one, by the way.)

The Cubs will win it all in 2009 because?

Bring me Jake Peavy and we’ll talk.

The Cubs won't win it all in 2009 because?

Wrong guy to ask that question.-------------------------------------------------------------------

Greg Maddux flirted with me once while he was signing an autograph for my daughter Theresa. But I knew it wasn’t worth pursuing because a) he was already married; and b) I’d read somewhere that his all-time favorite dinner was meat loaf and meat loaf makes me gag.

WHO WERE YOU?:

Probably Mike Harkey. I was usually a high draft pick because my brother and sister were killer athletes, but it was always a mistake to sign me because I never lived up to the perceived potential (I throw like a girl) and I got injured a lot.

WORKING ON:

A short story collection and a novel about a lawyer who discovers she’s HIV positive (and her husband is not) when their infant daughter is diagnosed with AIDS and subsequently dies. I wanted to explore the idea of how a good mother who inadvertently kills her child could work through anger and grief and guilt and get to a point where she feels like she has something to offer the world again. But I’m trying to add some comedic elements into the storyline so that my family and friends will read it.

DAY JOBS:

Freelance writer, adjunct fiction writing instructor at Columbia College Chicago and co-founder and co-host of Dating for Nerds (board game and trivia parties for smart singles).

WRITER I’D HIRE TO MANAGE THE CUBS:

Douglas Adams (R.I.P.), who could create a parallel universe in which the Cubs reign supreme.

THE CUB I’D MOST WANT TO LIVE INDEFINITELY IN MY BASEMENT: Andre Dawson. My daughter lives in Los Angeles now and I’m always looking for ways to lure her back home without sounding too needy.

MOST CHERISHED CUBS MEMORY:

The summer of ’92, my dad was given four tickets to a Cubs game that included a pre-game brunch in the stadium club and he and my mother took my daughter (who was 12 at the time) and me. They had never been to a baseball game before, so we were really excited about introducing them to the wonders of Wrigley Field, but they were more excited about the brunch. While I was in the bathroom, my daughter asked my mother about her attractive-looking orange juice in the fancy glass, so my mother said, ‘here, try it.’ It was actually a mimosa. By the time we went out to our seats, my daughter was complaining of a headache, and by the third inning, she fell asleep in her seat. While she was snoring away, I was yelling at my mom for feeding my daughter booze and she said, ‘you know, if you don’t make a big deal out of it, it won’t be a big deal to her when she’s a teenager.’ I hate to admit it, but my mother was right. And my parents are both gone now, but I think back often to how they made an effort to take an interest in what was important to Theresa and to me. I loved that day.

BEST PIECE OF CUBS MEMORABILIA:

We used to have a Shawon-O-Meter T-shirt, but I have no idea what happened to it.

THE CUBS WILL WIN IT ALL IN 2009 BECAUSE:

Sam Zell will eliminate September and October from the calendar to lure prospective buyers into thinking they’ll get a winning team.

To my knowledge the closest I've come to a Cub is when I sat five rows behind the plate at Wrigley in a game against the Dodgers in 1985.

Who Were You?:

I was Eddie Mathews; I loved the Milwaukee Braves of the fifties when I was growing up in Marion, Iowa.

Working On:

An article on basketball. I recently started shooting hoops again after 30 years. I can shoot with either hand and this got me into trouble once in the seventies when I was showing off to a bunch of strangers who took umbrage and reacted violently. I paid for the sin of pride.

Day jobs:

I've had about 25 jobs in my life, if you include gigs in the Air Force and Peace Corps. If success is defined by quantity, my professional career has been sterling; if it's defined by professional advancement, I'm an abject failure--but a happy one.

Literary figure I'd hire to manage the Cubs:

Yossarian.

The Cub I'd most want to live in my basement:

I wouldn't want anyone to live in my basement, even a hypothetical Cub.

Most Cherished Cub Memory:

When I was about 10 years old, my dad and mom and my sisters were in the car in Cedar Rapids, when we turned a corner. On a big billboard there was an advertisement for "CUB MOVING AND STORAGE." Already in love with baseball, when I saw that word Cub, I got a thrill.

I worked as a baseball columnist for nearly a decade and thus conducted many interviews in the locker rooms at Wrigley. It smelled worse than you can imagine.

Who were you:

That’s funny…I don’t ever remember assuming a player’s identity. Maybe I wanted to be Glenn Beckert, because I was small and scrappy and sometimes got into fights and couldn’t hit for power. What I really wanted to do was turn the double play. My playing career ended at about age 13.

Working on:

Just finished writing Pink Floyd FAQ, a book about one of the world’s weirdest and most avant-garde superstar bands. It’s coming out in May 2009. Currently I am editing Fantasy Baseball Index magazine, working on Who’s Who in Baseball 2009, and writing up some proposals for a couple more rock and roll books. I’m also a freelance editor and proofreader and I play in a rock band: The Captain Blood Orchestra.

Day jobs:

See above.

Literary figure I'd hire to manage the Cubs:

Sisyphus or Holden Caulfield.

The Cub I'd most want to live indefinitely in my basement:

Fergie Jenkins, no question.

Most cherished Cubs memories:

Maybe coming home from school at St. Jerome’s in 1970 and 1971, just a tyke, and going down to the Sheffields’ apartment (the elderly couple that owned the building we lived in), sitting on their sofa, and watching the last two or three innings of the game on WGN-TV. Also, my first game in 1971, and the 1984 division title.

Best piece of Cubs memorabilia:

During my childhood I wore out two copies of the Jack Brickhouse-narrated Great Moments in Cubs Baseball record album. The 1969 Cub Power LP is pretty special. My friend David Altman gave me a “Cub Power” button from ’69 that’s really neat.

The guy Hillmann is talking about is Moises Alou. We were with Irvine Welsh and Marty Tunny, leaving the Park West after Bill’s fight, when we saw Alou - on a side street - walking some kind of mincing little shaved teacup poodle. Irvine and Marty are Sox fans and ruthlessly opportunistic Cubs haters, so it was kind of embarrassing. The guy was so friendly and gracious, though, that even they didn't have a bad word to say about him.

WHO WERE YOU?:

I was Bruce Sutter. I couldn't throw a split-finger, but I did strike out a few fellow Little Leaguers.

WORKING ON:

Finishing upa novel called Reel Shadows, and a couple of screenplays.

DAY JOB:

Columbia College Fiction Writing Department.

LITERARY FIGURE I’D HIRE TO MANAGE THE CUBS:

Tantalus.

THE CUB I’D MOST WANT TO LIVE INDEFINITELY IN MY BASEMENT:

None of them. Christ. The off-season is for forgetting.

MOST CHERISHED CUBS MEMORY:

Bill Madlock went 4-for-4 on the last day of the season to just barely squeak by Ken Griffey, Sr. (who went 0-for-2) and win the batting title.

BEST PIECE OF CUBS MEMORABILIA:

About six months ago, I saw a Cubs hat at CVS for two dollars. I figured, what the hell, I can always use another Cubs hat. When I got home, I tried it on. It had a really tall crown and I looked like an idiot. No wonder it was two dollars, it was the dorkiest Cubs hat ever made. Later that night, a girl came over to my apartment. I pointed to the hat and said: "I got you something." She tried it on and it was ridiculously huge on her. "The minute I saw that hat," I told her, "I just knew it would look unbelievably cute on you." She went and stared in the mirror for about 30 seconds, and then turned to me with this astonished smile and said: "You're a genius. How did you know?" I just shrugged. About 10 minutes later, I found her waiting for me in bed wearing nothing but a pair of panties and the hat. "Geez," I thought, "she really likes that hat." Later, she started analyzing it all for meanings. She gazed at me through narrowed eyes. She concluded that I was: "kind of a pervert."

THE CUBS WILL WIN IT ALL IN 2009 BECAUSE:

You can't beat the odds forever.

THE CUBS WON’T WIN IT ALL IN 2009 BECAUSE:

Once they get into the playoffs, the media will bombard the players with an unavoidably disproportionate amount of attention. The whole circus--all the talk of curses and how wildly jubilant Chicago will be once the Cubs finally win the World Series, and how crushed everyone will be if they blow it--will spook the team once again. By the time the first playoff game starts, even the most hardened veteran will walk out onto the field with the rubbery legs of a newborn colt, and the Cubs will extend their post-season streak to an even dozen.

Sixth grade, with my dad, Terry Webb, who certainly fulfilled his paternal duty by taking me to Wrigley instead of some much more appreciative and Cubs-rabid friend on that day long ago.

Who were you:

Ron Cey, because I thought penguins were cute and always felt bad that he was best known for his pop-ups during crucial moments in the game.

Working on:

Lots of stories, a novel, my abs and triceps.

Day jobs:

Corrupting young, Facebook-addled minds at two Chicago universities.

Literary figure I'd hire to manage the Cubs:

Studs Terkel (RIP) – he would have been great, no?

The Cub I'd most want to live indefinitely in my basement:

Ryne Sandberg – he’s still cute (I think?) and could probably open the pickle jars when I couldn’t get past that damn vacuum seal.

Most cherished Cubs memories:

Uh….

Best piece of Cubs memorabilia:

Double uh…

The Cubs will win it all in 2009 because:

Lou Pinella has a fine team of talented players and is a smart, level-headed guy (at least he has been when I’ve heard him on AM 1000 during interviews – which, believe it or not, I’ve heard because my boyfriend makes me listen to sports radio in the car sometimes).

I heard from a friend of a friend that Lou Piniella read my Gehrig bio.

Who (baseball player) were you (when you played as a kid):

Bobby Murcer.

Working on:

A tight deadline for my new Capone book.

Literary figure I'd hire to manage the Cubs:

Ahab, no doubt about it.

Most cherished Cubs memories:

The day after my daughter was born, I snuck out of the hospital while my wife slept and went to the ballpark to catch a few innings of the Yankees and Cubs, with Clemens trying for—and failing to get—his 300th win. Unfortunately, I failed to make it back before my wife awoke.